Beginner Sailing Vacation: Course, Skippered Charter or Flotilla?

If you have never sailed, there are three common ways to spend a week on the water. On a learn-to-sail course you join a small crew and an instructor teaches you to sail the boat yourselves. On a skippered charter you hire a boat with a professional skipper who sails it for you. On a flotilla, several boats sail the same route together and meet up in the evenings. All three let you wake up in a new anchorage every morning. The difference is how much you learn, how much you do, and who you spend the week with.

This is what we do at Sailing Virgins. You live aboard a cruising yacht of around 40 to 50 ft for a week, with 5 students per instructor, and sail from island to island. You steer, trim the sails, anchor and handle the lines from day one, and you can earn up to two ASA certifications if you want them. It is the best choice if you want to come home actually able to sail, and the most sociable one if you are travelling solo, because you join a crew of people who want the same thing. It is a shared boat, so you share a cabin unless you book one together, and the days are active. We run course weeks in 9 destinations, including the British Virgin Islands, Croatia and Greece.

On a skippered charter you rent a whole boat for your group, and a professional skipper sails it. You choose the pace: swim, snorkel, eat well and help with the ropes only if you feel like it. Many skippers are happy to show you the basics, but teaching is not the point of the week and there is usually no certification. It is the best choice for a family or group of friends who want a private boat and a relaxed holiday, and for anyone who wants to try life on a boat before deciding whether to learn. You will come home knowing whether you love it, but not knowing how to sail. We also run private boats for families and friend groups. The difference from a plain skippered charter is that your captain is one of our instructors, so the week can be as much or as little of a course as you like.

A flotilla is a group of boats sailing the same route, usually with a lead crew who plan the days and help if anything goes wrong. In many flotillas each boat is sailed by its own guests, so at least one person aboard needs to be able to skipper. Some flotillas add a skipper or an instructor on each boat, which makes them open to beginners. The best part is the social side: the whole fleet ends up in the same harbour every evening. It suits groups who want company beyond their own boat. Our own Greece flotilla has five catamarans on one route, each with its own instructor, so beginners can learn on it while the fleet sails together.

Choose a course week if you want to learn to sail properly, earn ASA certifications, or you are travelling on your own and want a crew. Choose a skippered charter if you want a private boat for your own group and a relaxed holiday where someone else does the sailing. Choose a flotilla if your group wants the social life of a fleet. If nobody in your group can skipper yet, pick one with an instructor or skipper on every boat. Still not sure? Tell us who is coming and what you want from the week, and we will tell you plainly which option fits, even if it is not one of ours.